Phospholipids are known to be a component of a biomembrane. Phosphatidylcholine, one of phospholipids, is a glycerin ester of a long chain alkylcarboxylic acid having a phosphorylcholine group in polar part thereof.
Recently, some attempts have been made to synthesize a phospholipid-like compound having the phosphorylcholine group. For example, there is known a method for producing the objective phosphorylcholine derivative by reacting 2-chloro-2-oxo-1,3,2-dioxaphosphorane (sometimes referred to hereinbelow as "COP") with a compound having a hydroxyl group in the presence of a tertiary amine such as triethylamine, which acts as hydrogen chloride catcher, to produce 2-oxo-1,3,2-dioxaphosphorane derivative; and then reacting the resulting derivative with trimethylamine (Bull. Soc. Chim. Fr., p667-671, 1974, C. R. Acad. Sc. Paris, t.283 Serie C, p229-231, 1976, Zh. Org. Khim. 16(1), p31-33, 1980, C. R. Acad. Sc. Paris, t.275 Serie C, p1125-1127, (1972)).
There is also known a 2-((meth)acryloyloxy)alkyl-2-(trimethylammonium)ethyl phosphate (sometimes referred to hereinbelow as "(M)APC") having the phosphorylcholine group and a (meth)acryloyl group introduced thereto as a polymerizable group. Methods for producing this "(M)APC" and 2-(2-oxo-1,3,2-dioxyaphosphoryl)alkyl (meth)acrylate, an intermediate product of this "(M)APC" (sometimes referred to hereinbelow as "OP(M)A"), have also been proposed.
For example, it is known that the intermediate product "OPMA" may be produced by reacting 2-hydroxyethyl methacrylate with "COP" in the presence of a tertiary amine, and removing the by-product, that is, hydrochloride of the tertiary amine. It is also known that "MAPC" may be produced by reacting the obtained "OPMA" with a tertiary amine such as trimethylamine (JP-B-2-49316, and WO95/14702 specification). However, in these production methods, it is difficult to sufficiently remove the by-product due to the tertiary amine, which has been used as the hydrogen chloride catcher. In addition, the reaction liquid and the objective "(M)APC" tend to be colored in pale yellow or dark brown. Further, the reaction rate is not sufficiently fast.
Then, it has been proposed to perform reaction under reduced pressure in the absence of a tertiary amine (JP-A-8-239394). However, in this method, hydrogen chloride gas is generated as a result of the reaction under the reduced pressure. It takes a long time to remove the gas. Further the reaction results in low reaction ratio.
It has also been proposed to produce "(M)APC" by reacting 2-hydroxyethyl methacrylate with "COP" using specific acetonitrile in the presence of triethylamine, and then opening the ring by reaction with trimethylamine, and optionally re-crystallizing the product from dry acetonitrile (JP-A-9-505578). However, the coloring of the reaction liquid and the product also occurs in this method. Thus, for producing, e.g., a contact lens by polymerizing the obtained "(M)APC", it is required to perform the step of removing the coloring substance from "(M)APC", such as absorption by activated charcoal, re-crystallization or column chromatography, and the production step cannot therefore be simplified.